


There's a First Time for Everything

by bottomsub_dean (orphan_account)



Category: Supernatural
Genre: Alternate Universe - Human, Anal Fingering, Anal Play, Ankle Cuffs, BDSM, Bisexual Dean Winchester, Bondage, Club Owner Castiel, Communication, Crying, Dom Castiel, Dom/sub, Dominant, Enthusiastic Consent, First Time, First Time Bottoming, Gentle Dom Castiel, Human Castiel, Kissing, M/M, Master Castiel, Pain, Praise Kink, Rimming, Safe Sane and Consensual, Safewords, Size Kink, Sub Dean, Submissive, Top Castiel/Bottom Dean Winchester, and dean's as is super tight, cas has a big dick, kink club au, thus some mild pain
Language: English
Status: Completed
Published: 2017-06-05
Updated: 2017-06-05
Packaged: 2018-11-09 04:46:22
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,091
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11097189
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/bottomsub_dean
Summary: Based on a tumblr dialog prompt!#128 “You’re beautiful, you know that?”





	There's a First Time for Everything

**Author's Note:**

> Follow me on tumblr and I'll love you forever.

“You’re beautiful, you know that?”

“Uh,” Dean said, rubbing the back of his neck, “thanks.” He had been called many things in his life – hot, handsome, sexy – but beautiful? That was a new one.

The too-gorgeous black-haired man in front of him smiled genuinely. “I’ve never seen you here before,” he said.

Dean chuckled nervously. “Yeah, well, I’ve never had the stones, I guess.”

The other man laughed, and his eyes squinted slightly as he did. “It’s really not as scary as people expect. I think some hear ‘BDSM club’ and think they’re going to be pushed into something crazy right away.” He shook his head, seeming disappointed. “If only people would just read my policy on keeping everything that happens here safe, sane, and consensual.” When Dean frowned and looked confused, the man’s brilliant blue eyes widened. “Oh, I’m sorry! My name’s Castiel Novak. I own the club.”

The younger man stuck out his hand for Castiel to shake. “Oh, wow. Hi, I’m Dean Winchester.”

The owner’s face remained kind and void of any judgement. “Hello, Dean.” After a silence that was almost too long, the man spoke again. “Do you have a partner?”

Dean was taken aback by the question. “Uh, no, actually.”

Castiel’s eyes flickered with an emotion Dean couldn’t place. “May I buy you a drink then? Perhaps we could go sit on the couches in the corner and get to know one another.”

The freckle-faced man had expected to have one drink and some awkward conversation before he excused himself with a lie about an having early day tomorrow. Instead, roughly two hours later, Dean was nowhere near being ready to leave.

The two were sitting closer together than they had been originally. Castiel turned his body toward the other man slightly, his face almost glowing from the laugh he’d had at one of Dean’s jokes. He seemed to be leaning forward. “You really are a beautiful man, Dean Winchester,” he said quietly, so much so that it made Dean realize just how close they were. Their faces were mere inches part, and Cas was gradually leaning in to close the gap.

When their lips touched, it was soft and gentle. Slowly, the kiss became more heated until Cas’s hands were cupping Dean’s face and Dean was beginning to pull him back onto the couch with him. Before they were fully horizontal, though, the club owner pulled away.

“I have a play room in the back,” he started breathlessly. He placed another kiss on the waiting pair of lips below him. “It’d be a little more comfortable.” When Dean hesitated slightly, he added, “We won’t do anything you don’t want to do, I give you my word. The motto’s ‘safe, sane, and…’”

“Consensual,” Dean finished, maybe feeling a bit _too_ at ease with Castiel. When he shifted to get up, his hard-on rubbed against the inside of his jeans, causing him to groan. “Okay, yeah, let’s go.”

The owner smirked before taking Dean’s hand and leading him through the crowd and into the back hall of the club. There was a line of about six doors, all with name plates on them. The younger man admired them and the titles of Master, Mistress, Miss, and Sir engraved into the metal. It was obvious, even from the outside, that the room on the end was by far the largest. The reasoning made sense when the name plate read _Master Castiel Novak (Owner)_. Though he had had his suspicions, the confirmation of Castiel’s undoubtedly dominant nature sent a wave of excitement over Dean.

The messy haired man unlocked the door and motioned for Dean to enter. The man didn’t have time to register anything other than a bed inside before the door was closed and he was being pressed against it. Lips attached to his, and he kissed back before he was being torn away from the door and manhandled onto the king-sized bed.

“What’re your safewords?” Cas asked suddenly, standing at the end of the bed and staring down at Dean once he was on his back. His expression still showed the kind, trustworthy man Dean had been talking to before but now there was an added element of _I’m in charge_.

“I- I don’t..” Dean took a deep breath and started again. “The traffic light system works for me.”

Castiel gave him a look. “Can you tell me what the traffic light system is?”

“Green to go. Yellow to slow down and check in. Red to stop everything.”

“Good boy,” Cas mused and the other man felt a momentary flutter in his chest. “Have you ever had a Dom before?” 

Dean shook his head and lowered his eyes, completely convinced his lack of experience was a disappointment to the other man. Though he had done extensive research into the BDSM lifestyle, he had never actually lived it. He waited for an order telling him to leave, but it never came.

“Dean, look at me.”

He did.

“Good. Are you submissive?” The question was more out of curiosity than anything.

“Yes, Sir.”

Castiel’s eyes darkened. “Careful, boy. Keep that up and you might be getting fucked tonight.” A playful smirk pulled on the Dom’s lips and Dean’s dick grew impossibly harder in his pants. He just barely resisted the urge to squirm.

“That’s the idea.” The sub winked.

Castiel chuckled. “Is it now? Well then, I want you to strip, fold your clothes, and then sit back on the bed for me.”

The Winchester obeyed quickly. Within moments, he was back on the bed and everything hit him. He was really about to submit to the owner of this club. He was about to actually _bottom_ for the first time in his life. He hadn’t started experimenting with his bisexuality until just months before, and though he had slept with men before, he had never felt comfortable enough with someone to do anything but top. Of course, he’d fantasized about having something in his ass, but since he lived with his nosey little brother, owning sex toys was out of the question.

A hand on his cheek brought him back to reality. “Hey. What’s wrong?” The Dom’s blue eyes were caring and concerned.

The younger man blushed and tried to stare at his lap, but fingers caught his chin and forced him to look up. He sighed. “I’m sorry. I’ve just never… done this before.”

“Submitting to someone is a very brave thing to do, Dean. I understand if you’re nervous.”

Dean shook his head. “No, no, it’s not that. I trust you. I just… I’ve never bottomed before either.”

Cas smiled kindly, though he did look a little surprised. “That’s okay too. What experience have you had? Anything you’ve done by yourself? Have you ever slept with another man?”

He nodded. “Yes, Sir, I have. And all I’ve ever used by myself was a finger, but I don’t own much in the way of lube.”

“I see. What’s your color?”

“Green.”

Finally, the Dom moved to remove his own clothes, which consisted of a blue dress shirt, black slacks, and a blue tie. When he was completely naked, he climbed onto the bed so that he was hovering over him. The tender kiss he pressed to Dean’s lips had the sub’s nerves dissipating immedietely. Their kisses transformed into making out with light humping, all while Cas pinned Dean’s wrists to the bed. Eventually, Castiel kissed down Dean’s body, muttering praises the whole way.

“Get on all fours for me, sweetheart,” the older man instructed once his lips had kissed over Dean’s hips. When he did, Castiel muttered a “good boy” before saying more loudly, “Stay on your knees, but put your weight on your chest. Perfect. Now reach back and spread yourself open for me. I want to see that hole. Absolutely **_beautiful_**.”

Dean’s whole body felt too warm, but he didn’t have time to worry too much about it because Cas started licking long stripes over his exposed entrance. All he could do was close his eyes and moan. He then heard the sound of a bottle opening and then cold, thick liquid was being poured down his crack. The cool sensation didn’t last long, though, because Castiel’s hand was stroking his hole and smoothing it around. After a few moments, a single finger pushed in. A low whine escaped him.

“You’re so tight,” Castiel observed, his voice making him sound totally awestruck. He moved his finger around a little before pushing a second finger in. That time, there was a slight burn at the stretch and Dean sucked in a sharp breath. “Color?”

“Green.” 

Castiel continued using his fingers to scissor and stretch Dean’s hole until he felt like he was ready. “Turn over, baby,” Cas ordered then. He moved expertly around the bed as the sub waited on his back for his next command. Cas went to the headboard and grabbed two pieced of black rope that were tied to the same piece of circular metal that seemed to be secured to the headboard. At the ends of the rope were plush-looking leather cuffs. “I’m going to fasten these to your ankles. Is that okay?”

The other man nodded, still not sure how he hadn’t noticed the cuffs before.

“I need a real answer, Dean.”

“Yes, Sir, that’s okay.”

Cas lifted Dean’s legs to buckle the cuffs around them, making sure he could slip two fingers under the leather so it wouldn’t be too tight. Once they were done, Dean’s legs remained raised and his hips slightly elevated, as there wasn’t enough give in the rope to allow him to lower them.

“You’re such a good boy, Dean,” Cas breathed, running his hands up and down Dean’s legs once he was positioned between them. “So, so beautiful. Still green?”

“Yes, Sir.”

“Perfect.”

The lid of the bottle snapped open again, and Cas was rubbing lube on his intimidating erection that he had covered with a condom. The man must have registered the tensing of Dean’s body because he locked eyes with the sub and pressed a kiss to his inner thigh.

“It’s okay, baby. Just relax.” The tip of his cock glided over Dean’s hole and drew out a moan before he was pushing himself in oh so slowly.

“ _Ooh!”_ The sub whined at an embarrassing volume when the head pushed past his rim. He threw his head back and closed his eyes. “ _Fuuuck_.”

Castiel pushed in a little bit further, and Dean gasped and whimpered and moaned. He felt like he was being split open. Despite the copious amount of lube, it still burned. With the next twitch of Cas’s hips, the younger man’s hands flew up to grip the Dom’s shoulders.

Tears brimmed his eyes. “Ow,” he winced. “Cas. Sir. Yellow.” A single tear rolled down his cheek. “Your cock.. It’s too big.”

Immediately, Castiel dropped down so that his hands could slide underneath Dean’s head and neck, careful not to move his pelvis too much. “Shhh, sweetheart, I know. I’m sorry.” He kissed Dean’s pouting lips. “You’re okay. I’m going to make you feel so amazing, I promise.” His hand dropped and helped guide his dick into Dean by couple more inches, earning a whine. “I’ve got you,” Cas whispered against parted pink lips. “I’m gonna take care of you.”

The submissive squeezed his eyes shut and continued to just barely return Castiel’s heated kisses. After Dean had relaxed more, he pushed in the rest of the way.

Dean cried out and Castiel pulled back and thrust in again. He did so a couple times as he heard Dean’s sounds transform from cries of pain to desperate moans. The noises sparked a fire in him and he began thrusting faster, nailing the sub’s prostate relentlessly.

“Fuck, fuck, fuck,” Dean huffed breathlessly as Castiel rolled his hips with a grunt. Tears were streaming down is face now.

“You feel so fucking good,” Cas praised. “So amazing.”

“Shit, _Castiel,”_ the sub whimpered. “I’m… Fuck, I’m gonna..” The warning wasn’t even out of his mouth before he screamed into Cas’s mouth and both of them were being covered in his release. That was enough to send the Dom over the edge and he came too, holding Dean’s shaking form close.

After he disposed of his used condom, Cas cleaned them up and released Dean’s legs. He then grabbed some juice from his mini fridge and had Dean drink as much as he could before the two cuddled up together and fell fast asleep.


End file.
